Dimethyl Sulfide → 2-(2-Fluoro-4-nitrophenyl)ethan-1-ol

To a stirred solution of 2-(2-fluoro-4-nitrophenyl)acetic acid (1 g, 5.02 mmol) in tetrahydrofuran (10 mL) was added BH3.S(CH3)2 (7.5 mL, 7.53 mmol) at 0° C. The reaction mixture was allowed to stir at room temperature for 10 h. Then reaction mixture was cooled to 0° C. and the excess of borane was quenched with methanol (10 mL). The reaction mixture was concentrated under reduced pressure to obtain a crude compound which was purified by CC (eluent: ethyl acetate/n-hexane (1:1)) to give 2-(2-fluoro-4-nitrophenyl)ethanol (0.89 g, 95%).

1. customat 0° C
2. customThen reaction mixture
3. temperaturewas cooled to 0° C.
4. customthe excess of borane was quenched with methanol (10 mL)
5. concentrationThe reaction mixture was concentrated under reduced pressure
6. customto obtain a crude compound which
7. customwas purified by CC (eluent: ethyl acetate/n-hexane (1:1))

ORD record

ord-234fce0a78ea40c5ab88601b6346fd1e

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08946204B2